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Effect of Alkyl Group on Transnitrosation of N-Nitrosothiazolidine Thiocarboxamides
https://repo.qst.go.jp/records/48526
https://repo.qst.go.jp/records/48526d4b5b2b7-dd94-47ea-a6f8-e91d5d431cfb
| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2018-02-20 | |||||
| タイトル | ||||||
| タイトル | Effect of Alkyl Group on Transnitrosation of N-Nitrosothiazolidine Thiocarboxamides | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 著者 |
Inami, Keiko
× Inami, Keiko× Ono, Yuta× Kondo, Sonoe× Nakanishi, Ikuo× Ohkubo, Kei× Fukuzumi, Shunichi× Mochizuki, Masataka× 稲見 圭子× 中西 郁夫× 大久保 敬 |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | S-Nitrosoglutathione (GSNO) relaxes vascular smooth muscles, prevents platelet aggregation, and acts as a potential in vivo nitric oxide donor. 3-Nitroso-1,3-thiazolidine- 4-thiocarboxamide (1), a N-nitrosothioproline analogue, exhibited a high GSNO formation activity. In this study, two compounds (2 and 3) based on compound 1 were newly synthesized by introducing either one or two methyl groups onto a nitrogen atom on the thioamide substituent in 1. The pseudo-first-order rate constants (kobs) for the GSNO formation for the reaction between the compound and glutathione (GSH) followed the orde 1 > 2 ≈ 3. Thus, the introduction of a methyl group(s) onto the thioamide group led to a decrease in the transnitrosation activity. On the basis of density functional theoretical calculations, the transnitrosation for the N-nitrosothiazolidine thiocarboxamides was proposed to proceed via a bridged intermediate pathway. Specifically, the protonated compound 1 forms a bridged structure between the nitrogen atom in the nitroso group and two sulphur atoms–one in the ring and the other in the substituent. The bridged intermediate gives rise to a second intermediate, in which the nitroso group is bonded to the sulphur atom in the thioamide group. Finally, the nitroso group is transferred to GSH to form GSNO. | |||||
| 書誌情報 |
Bioorganic & Medicinal Chemistry 巻 23, 号 20, p. 6733-6739, 発行日 2015-09 |
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| 出版者 | ||||||
| 出版者 | Elsevier | |||||
| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0968-0896 | |||||
| PubMed番号 | ||||||
| 識別子タイプ | PMID | |||||
| 関連識別子 | 26386820 | |||||
| DOI | ||||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1016/j.bmc.2015.09.008 | |||||
| 関連サイト | ||||||
| 識別子タイプ | URI | |||||
| 関連識別子 | http://www.sciencedirect.com/science/article/pii/S096808961530033X | |||||
| 関連名称 | http://www.sciencedirect.com/science/article/pii/S096808961530033X | |||||
